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β-萘酚的不对称去芳构化通过双功能硫脲催化的迈克尔反应实现。

Asymmetric Dearomatization of β-Naphthols through a Bifunctional-Thiourea-Catalyzed Michael Reaction.

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/.

出版信息

Angew Chem Int Ed Engl. 2015 Dec 1;54(49):14929-32. doi: 10.1002/anie.201507998. Epub 2015 Oct 14.

Abstract

An intermolecular asymmetric dearomatization reaction of β-naphthols with nitroethylene through a chiral-thiourea-catalyzed Michael reaction is described. Enantioenriched functionalized β-naphthalenones with an all-carbon quaternary stereogenic center could thus be easily constructed from simple naphthol derivatives in good yields and excellent enantioselectivity (up to 79% yield, 98% ee).

摘要

描述了一种通过手性硫脲催化的迈克尔加成反应实现β-萘酚与硝基乙烯的分子间不对称去芳构化反应。通过简单的萘酚衍生物可以高产率和优异的对映选择性(高达 79%的产率,98%ee)轻松构建具有全碳季立体中心的手性官能化β-萘满酮。

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